CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Car values
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Used Chevrolet Silverado 1500 LT Trail Boss for Sale near Monroe, WI

356 results
Monroe, WI
2022 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD Lenz Truck Center

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

45,139 miles

$39,891

Good Deal
Fond du Lac, WI
99 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Summit White
Interior color:
Black
Transmission:
Automatic
Mileage:
45,139
Stock number:
YB34140
VIN:
3GCPYFED9NG103815

Sponsored

2023 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

62,894 miles

$39,991

Good Deal
Sycamore, IL
64 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
62,894
Stock number:
39P1495
VIN:
3GCUDFED3PG338731

Sponsored

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

44,347 miles

$39,725

Fair Deal
Elmhurst, IL
98 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Gray (Satin Steel Metallic)
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
44,347
Stock number:
P5844
VIN:
1GCPYFED7MZ447271

Sponsored

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

65,585 miles

$34,998

Good Deal
Certified Pre-Owned
Harvard, IL
53 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Silver Ice Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
65,585
Stock number:
25242A
VIN:
1GCPYFEDXMZ105359

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

78,080 miles

$34,979

Fair Deal
Milton, WI
37 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Shadow Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
78,080
Stock number:
1610A
VIN:
1GCPYFED3MZ124903

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

78,380 miles

$34,945

Fair Deal
Orfordville, WI
18 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
78,380
Stock number:
P7559A
VIN:
1GCPYFEL4LZ379680

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

14,325 miles

$53,975

Fair Deal
Walnut, IL
73 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Gray
Combined gas mileage:
25 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
14,325
Stock number:
4442A
VIN:
3GCUDFE85RG266386

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

10,730 miles

$54,495

Good Deal
Certified Pre-Owned
Naperville, IL
94 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Cypress Gray
Combined gas mileage:
23 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
10,730
Stock number:
K6987
VIN:
3GCUKFE89SG246184

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

10,115 miles

$46,918

Fair Deal
Certified Pre-Owned
Cedarburg, WI
96 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Red Hot
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
10,115
Stock number:
26131A
VIN:
3GCUDFEL4NG505103

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

65,509 miles

$41,490

Good Deal
Elgin, IL
78 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
65,509
Stock number:
P2893
VIN:
3GCUDFED5RG159187

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

54,493 miles

$37,598

Good Deal
Certified Pre-Owned
Milwaukee, WI
89 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
54,493
Stock number:
C19521N
VIN:
1GCPYFEL8MZ366769

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

40,506 miles

$38,882

Great Deal
Lake Geneva, WI
61 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Cherry Red Tintcoat
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
40,506
Stock number:
30T1419A
VIN:
1GCPYFEL0MZ419075

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

47,105 miles

$41,900

Good Deal
Byron, IL
38 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
47,105
Stock number:
S1592
VIN:
1GCPYFED5NZ161467

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

59,812 miles

$34,999

Fair Deal
Hoffman Estates, IL
87 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Shadow Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
59,812
Stock number:
PM5700AA
VIN:
1GCPYFED3LZ106738

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

47,361 miles

$37,977

Fair Deal
Certified Pre-Owned
Milwaukee, WI
89 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
47,361
Stock number:
C19605NC
VIN:
1GCPYFED0LZ297695

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

9,349 miles

$55,425

Good Deal
Certified Pre-Owned
Baraboo, WI
62 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Summit White
Combined gas mileage:
23 MPG
Fuel type:
Diesel
Interior color:
Jet Black, Leather-appointed front outboard seatin
Transmission:
Automatic
Mileage:
9,349
Stock number:
41668A
VIN:
3GCUKFE88SG318802

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

55,268 miles

$36,997

Fair Deal
Fond du Lac, WI
99 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Gray (Satin Steel Metallic)
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
55,268
Stock number:
B35439
VIN:
3GCPYFED8LG413015

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / LT Trail Boss
  5. / Wisconsin
  6. / Monroe
  • Chevrolet Silverado 1500 LT in Monroe WI

  • Chevrolet Silverado 1500 RST in Monroe WI

  • Chevrolet Silverado 1500 LTZ in Monroe WI

  • Chevrolet Silverado 1500 LT Trail Boss in Monroe WI

  • Chevrolet Silverado 1500 LT1 in Monroe WI

  • Chevrolet Silverado 1500 Custom in Monroe WI

  • Chevrolet Silverado 1500 High Country in Monroe WI

  • Chevrolet Silverado 1500 Custom Trail Boss in Monroe WI

  • Chevrolet Silverado 1500 Work Truck in Monroe WI

  • Chevrolet Silverado 1500 in Janesville WI

  • Chevrolet Silverado 1500 in Madison WI

  • Chevrolet Silverado 1500 in Rockford IL

  • Chevrolet Silverado 1500 in Dubuque IA

  • Chevrolet Silverado 1500 in Clinton IA

  • Chevrolet Silverado 1500 in Palatine IL

  • Chevrolet Silverado 1500 in Davenport IA

  • Chevrolet Silverado 1500 in Aurora IL

  • Chevrolet Silverado 1500 in Kenosha WI

  • Chevrolet Silverado 1500 in Monroe WI

  • Old Chevy Trucks for Sale in Monroe WI

  • Classic Muscle Cars for Sale in Monroe WI

  • Chevrolet Trucks For Sale in Monroe WI

  • Cheap Muscle Cars for Sale in Monroe WI

  • Work Trucks for Sale in Monroe WI

  • Reliable Cars For Sale in Monroe WI

  • American Made Trucks For Sale in Monroe WI

  • Best Pickup Trucks For Sale in Monroe WI

  • Best Cars Under $5,000 For Sale in Monroe WI

  • 2019 Chevrolet Silverado 1500 LT Trail Boss in Monroe WI

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • Used Hatchbacks for Sale with Low Mileage

  • Used Convertibles for Sale with Low Mileage

  • Used Vans for Sale with Low Mileage

  • Used Minivans for Sale with Low Mileage

  • Used Pickup Trucks for Sale with Low Mileage

  • Used Coupes for Sale with Low Mileage

  • Used Wagons for Sale with Low Mileage

  • Kayser Chevrolet Buick GMC

  • Kayser Chevrolet Sauk City

  • Brodhead Automobiles

  • Hallada Auto Group

  • Symdon Chevrolet

  • Ed Morse Chevrolet

  • Bud Weiser Motors

  • Bergstrom Chevrolet of Madison

  • Bocker Chevrolet GMC, Inc.

  • Bergstrom Chevrolet of Middleton

  • Zimbrick Chevrolet

  • Burtness Chevrolet

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2026 CarGurus, Inc., All Rights Reserved.